A Kiss in the Night
by Shukumei-of-another-world
Summary: When Dean promises his angel friend that he won't die a virgin, he discovers that Castiel has far less experience than he thought. No way had this guy never been kissed. Dean takes it upon himself to right a wrong before they must summon Raphael. It's just a kiss – he can do that at least. Set during season 5, episode 3: "Free to Be You and Me"


**A Kiss in the Night**

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 **Disclaimer:** I do not claim to have any rights to the Supernatural franchise, its characters, script, etc.

 **Summary:** When Dean promises his angel friend that he won't die a virgin, he discovers that Castiel has far less experience than he thought. No way had this guy never been kissed. Dean takes it upon himself to right a wrong before they must summon Raphael. It's just a kiss – he can do that.

Set during season 5, episode 3: "Free to Be You and Me"

 **Author Notes:** This is my first Supernatural fanfic, and while I've only been a fan for a short time, I hope I did the characters some justice. I'm sure a lot of Destiel fans used this particular episode to their advantage; I know I did! I tried to use what I've learned so far from the series to address how a first kiss may played out between Dean and Castiel. (See more ramblings at end of story.) I appreciate kudos, reviews (constructive criticism is fine!), and bookmarks.

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It was near midnight by the time Dean and Castiel returned from what the angel had described as a "den of iniquity". Dean laughed at the proper title; it was a brothel. If Dean had a "nicer" title for it, he'd call it a gentleman's club, perhaps. His dear virgin angel friend had squirmed like a mouse surrounded by cats in there, and at that moment, Dean could not think of anything funnier. He had to admit that it was rather adorable, too, with the pleading and terrified look in Castiel's eyes. The damn Apocalypse was raining down on them, and an angel was shaken up by the possibility of a naked woman before him. Pushing that guy's buttons was a real pleasure; it was something that he sorely missed with his brother.

Dean tired to push thoughts of his brother aside; he had made his choice. Right now, Dean had to sit in the dark in a dingy cottage while he waited for the proper time to summon Raphael with the serious-as-a-heart-attack angel. At least with Sam, he'd have had something to talk about or research even. With Castiel, it was like talking to a rock sometimes.

It very well could be Castiel's last night on Earth. Last night _ever_ from Anywhere. Dean felt sorry for him, wanted to keep him occupied before he, the human, needed to catch a few hours of shuteye. If Cas was still up for it, they might be able to hit the town again to give him a night to remember.

Castiel sat quietly in a chair turned away from the table, his eyes seeming to bore holes into the window on the opposite wall. His hands sat loosely over his lap as his shoulders slouched with the impending weight of what could transpire tomorrow morning. He could probably use a break.

Dean cleared his throat as he leaned against a paint-chipped wall near the table behind Castiel. "Well, my pop-the-angel's-cherry plan backfired."

Castiel just stared ahead. That window must have been so fascinating.

Dean cleared his throat again, quieter, but as Castiel turned his head to him, Dean shrugged his shoulders. "Hey, don't look so disappointed. We've still got a few hours left to kill. I don't exactly have the cash to pay for another..."

Castiel's eyes narrowed.

"... lady of the night," Dean continued, thinking Castiel might not care for the word 'hooker'. He had no idea if that would have bothered him. "Maybe we can go to a bar and find a really drunk chick to at least make out with you. See where it leads?" Dean raised his brows with a cheeky smile.

Castiel turned away, shaking his head and lowering his eyes. "I wouldn't bother, Dean." His voice didn't sound disappointed, just completely serious.

Dean crossed his arms over his chest and scoffed. "What? I'm sure you could convince a girl to grope you in a dimly-lit bathroom. You're an Angel of the Lord for God's sake. Some girls would cream over that. Just, you know, don't tell them all the fine details."

"So lie?" Castiel asked, eyes never wavering from the window.

"Did you learn nothing from me earlier? Humans lie to get what we want. We have to find a drunk crazy one if you want to use the Angel card. Save her from getting hit by a car or even just from falling." Dean pushed away from the wall and held out his arms to mime cradling a woman with a bend at his waist. His voice took on a gruffer tone as he tried to mimic Castiel's raspy deep voice and said, "'My lady. I have been sent from the Heavens to protect you. May I assist you in seeking shelter?'" He stood back straight, holding up a finger in warning as his voice returned to normal. "No poofing her anywhere. You'd be a human pretending to be Angel, so you walk her where she needs to go, and see where the night takes you."

"But I'm not pretend-"

Dean put his hands out in front of him to stop Castiel from trying to explain. "I know, I know," he sighed. "What am I going to do with you? I told you that I don't want my friend to die a virgin. So, you haven't dallied in cloud-seeding. How far does your... purity go? Ever take care of business yourself?" That seemed far too cruel if that were truly the case.

Castiel lowered his head, and he hesitated as he admitted, "I... again, have not had the occasion."

Dean's eye widened in shock. Now he _really_ felt sorry for the guy. "Wow. That's... thousands of years of backed-up angel juice?" Or was it millions? Or billions?

Castiel said nothing.

Dean tried to get to the bottom of this and asked awkwardly, "Uh... any intimate contact of any kind?"

"Nothing of an intimate nature. No."

"That girl at the brothel, I paid for _nothing_?" Dean felt that he needed to sit down, so he went to the chair in front of Castiel and carefully eased his weight onto it. It wobbled and creaked in protest.

Castiel swallowed, taking in a deep breath, and pinched his tie a little more snugly around his neck. "She called me 'daddy' and attempted to remove my coat and tie."

Dean nodded and rehashed, "And then you decided to tell her about her own father?"

Castiel nodded back. "Yes, she gave implications that she was a bad daughter and that I should punish her." He tilted his head to Dean, a furrow in his brow and a slight frown forming on his lips.

Dean snorted, but sat back and tried to keep a straight face. "Huh. Did you?"

"Did I what?" Castiel looked like he really had no idea.

Dean wanted to shake his head. "Punish her."

Castiel narrowed his eyes and shook his head. He told him, "Clearly that was not the case, Dean."

Dean leaned forward, arms draped loosely over his thighs. He wondered what Castiel would have to say when he explained, "She was probably saying that she liked to be spanked."

Castiel looked down at his open palm. Dean couldn't imagine that the guy could look any more confused, but Castiel gave a slight grimace as he lifted his head again to regard him. Almost dumbfoundedly, Castiel asked, "Like a disobedient child?"

"Like a naughty, naughty girl." Dean could only smirk. Castiel had probably been around since the dawn of man, and he was really missing out on some of the more interesting perks of his human body. If he survived to tell the tale of the Calling of Raphael, the guy was in for a real treat.

Castiel closed his eyes and quietly groaned. "I do not understand her logic. Or yours, by your expression."

Dean shrugged, sitting back in his chair. Cas had a lot to learn; not even just about sex, but also the delicacies of interacting with humans – how not to get a girl to run from you shrieking about how much you're a jerk... Okay, so Dean, himself, might have needed a little work in that department, but once he had them, most women seemed to enjoy what he had to offer.

He decided to continue Castiel's lesson. "It's fun to get a little rough in the sack, sometimes. You know, play a role..." A realization hit Dean at that moment: he still hadn't gotten to the bottom of how 'pure' Cas really was. "Wait a God-damned minute! Did she even kiss you?"

Castiel simply said, "No."

Dean dropped his forehead into his palms. "You're hopeless," he said as he looked up pointedly at Castiel. "Please tell me you've done at least that with someone."

Castiel explained, "I have kissed my brothers and sisters-"

"Ew."

"-in a familial greeting," Castiel continued coolly, "but I presume that is not the answer you are looking for. No, I have not kissed anyone intimately as you have continued to ask."

The how-ever-many-years-old virgin was one thing, but to never have been kissed... It seemed so unreal to Dean. And cruel. Castiel had to be messing with him; it was the only explanation. 'He didn't have the opportunity' was a terrible excuse for a rebellious angel. "Why didn't you try to kiss her?" Dean prodded.

Castiel rolled his shoulders in a slight shrug. "I am unversed in such matters. I thought to let her lead, and I would follow."

Dean called bullshit on that. No way did the guy _not_ know how to kiss. "You've watched a movie, right? People making out in practically every one. Or even couples kissing on the street? Uh... dig through Jimmy's brain and pluck out memories with his wife?"

"Although Jimmy couldn't lie to me while I inhabited his body, I could only see what he revealed to me at that moment," Castiel answered, seeming to avoid the first questions altogether. "His memories were his own. I did not pry into his intimate affairs."

Dean whistled quietly, impressed. Castiel was still learning to keep out of physical personal space, but at least he was willing to draw a line somewhere. He had to admit that if he were to end up in someone else's shoes, he'd likely go poking around in their business – out of mere curiosity.

"Regardless," Dean ended up saying, "It didn't occur to you to plant one on her mouth?"

Castiel shook his head and confessed, "I did not feel inclined to."

"Uh... am I missing something? Women not do it for you?" Dean queried, knowing that neither a 'yes' or 'no' response would really surprise him. Castiel had clearly felt uncomfortable in the brothel, but had otherwise never shown an inclination towards either gender in the time that Dean had known him. No inclination towards any extracurricular activities for that matter. Dean wondered if the angel even had a _type_.

"I am an Angel, Dean," Castiel pointed out, "Gender is not a factor for us."

Dean snorted to himself; he had suspected as much. "I thought God was against the whole same-sex thing..."

Castiel clarified, his voice mostly monotone as if the words had no effect on him, "I cannot speak on what prophets have written regarding a man laying with another man, but Angels must follow other laws. We are not to feel. Feelings tend to incite disobedience which gets us punished or damned. Not least of all, we should not seek pleasures of the flesh."

"Oh, so, taking you to give it to some girl was a bad idea," Dean confirmed while scratching at his chin.

Castiel was quiet, and his eyes found the window in the dark of the room again.

Dean huffed, "You could have told me that."

"I might not survive the day. I entrusted my last moments... to your wiles," Castiel admitted, his voice hinting at a break under the pressure. "It would not be the first time that I rebelled."

Dean inquired, focusing his gaze on Castiel's eyes for any telltale sign of the man-beneath-the-wings, "So... are you even interested? In the 'pleasures of the flesh'?"

Castiel eyes moved up briefly, but fell back down, his face otherwise unchanging. "I am... curious, but I will accept my fate even if that curiosity is not sated."

Dean reached forward to place his hand securely on Castiel's shoulder. "Curious is good enough for me," he said, "Live a little, man. Let's head out as soon as we've set up here. Point out anyone that piques your interest on the way to St. Pete's, and I'll be your wing-man."

Castiel seemed to scrutinize his words and turned his head. "But I'm the one with wings."

Dean chuckled and shook his head. "It's what you call a bro that helps hook you up with someone," he explained, patting Castiel's shoulder. "It'll be great, Cas. I promise."

Castiel tilted his chin to look at Dean's hand on his shoulder. His gaze moved up to Dean, lingering.

It was Castiel's quiet and contemplative stares that always made Dean remember just how startlingly blue his eyes were – Jimmy's eyes, but they were innately Castiel's now. It was hard to tell in the dark, but the moon was nearly full, beaming light through the thin curtains, and Castiel's eyes were bright and clear.

Dean had to look away from those inquisitive eyes, worried that he had felt himself wanting to drown himself in them more times than he was comfortable to admit. "Or..." Dean dropped his hand back down to his waist, shrugging. "...We can sit here and go over the plan again. Up to you."

Castiel rubbed at the back of his neck, looking away as well. When he spoke, it almost sounded like a question, "You said anyone that piques my interest."

Dean shifted forward in his chair, leaning his weight into his hands balancing on his knees. "Yeah, yeah," he urged, "Anyone. Woman, man, beautiful, ugly as sin, old, young. I will draw the line at children though. And demons. Whatever else you want." Dean paused for a moment and shook his head. "No animals either. Just... covering the bases."

Castiel kept his gaze focused on his thumb rubbing circles almost nervously over his opposite palm. He had to clear his throat to speak. "There is one person."

Dean clapped his hands and stood up, pushing his chair away. "Alright, that's what I'm talking about! Then let's get going," he exclaimed.

Castiel shook his head, his voice betraying his resolve to keep a usual calm demeanor. "We don't need to go anywhere." It wasn't quite the deer-in-the-headlights look that he had had around the scantily-clad women, but the rigid set of his shoulders told Dean he might be encroaching on unfamiliar territory for Cas.

"You got them on speed-dial?" Dean asked, hoping the question was neutral enough.

Castiel nodded, fiddling with his hands in his lap. "Yes, but you knew that already."

"Then who...?" Dean stood in front of Castiel, starting to go over the list of numbers that Castiel would have in his phone. He only had reason to call himself or Sam. Maybe Cas had added numbers as he... no... _He wouldn't. Would he?_

"I struggle with understanding emotions," Castiel admitted, seeming to also struggle with the words. "I realize that I have begun to feel them, but I don't know how to act on them, usually. My feelings are muddled, unclear. This... _person_ helps me learn a little bit about being my own self. Accepts and understands my doubts. Makes me question orders when they are likely wrong."

"Cas?" Dean's face fell as he thought his chances of guessing said person were fifty-fifty. Pieces were falling into place, but Dean was still grasping at straws to come up with more names of those that Castiel had come into contact with.

"I would not ask it of them, Dean, because I know them." Castiel upturned his chin to set Dean with a somber gaze. "The answer would be 'no'."

Dean took in sharp breath, shaking his head. "You've got to be frickin' kidding me, Cas." He turned away and started to pace. "Me?" Of course it would be him. What Castiel was describing: there was hardly anyone else that fit the bill.

Castiel answered seriously, "Why not you?"

"I – I don't even know what to say," Dean stammered, shifting on his feet to face Castiel again. He honestly didn't. He could admit that he wasn't surprised, but _knowing_ it was a-whole-nother thing. "Really?"

Castiel answered, remaining in his chair, "Yes. You, uh, make me willing to try irresponsible and possibly exciting experiences. Like going to... brothels. I find it strange."

Dean pinched his brow, clenching his teeth. "You're... what? In love with me?"

Castiel watched Dean with a slight tilt to his head, lips parted and eyes almost unfocused, before he blinked and shook his head. "I wouldn't call it love, Dean. I told you, I don't understand what I'm feeling most of the time. This _feeling_ of care and concern for you. I'm unsure of what it means."

Dean gestured his arms wildly between them, barking out, "It means we're friends, Cas. I care for you, and I'm concerned as hell when something's wrong with you. It does _n_ _o_ _t_ have to mean _romantic_ love."

Castiel nodded, looking down at his hands. "That's probably it," he tried to agree, brows slightly furrowed. "The intensity of it surprises me some times."

 _Now_ Castiel sounded disappointed. He hadn't been when the prospect of bedding a woman was mostly out of the question. Castiel was battling with his emotions, and Dean knew he was lying when he said he'd be okay without satisfying his curiosity if this meant the end.

Dean turned away then, lost in thought for a time. They had the time to find someone for Castiel to hook up with had he been a normal and functional human being, but the guy was an awkward, nerdy mythical being that barely knew how to work a phone not too long ago. Dean didn't have a chance in hell to get Castiel laid tonight with all the bumbling and too-serious attitude that had no bedside manner. They would be hard-pressed to find someone that would be into that with such short notice.

So, someone that was readily available to take one for the team would need to step up to the plate. Which meant Dean had to consider if he was willing to kiss – _make out?_ \- with Castiel. The idea didn't make him cringe as much as he thought it would. Castiel was not his type, pretty far from it. The guy was annoying with his appearing and disappearing acts, dodging questions and avoiding clear answers; although, some of that was sort of fun – teaching him the ropes and watching him squirm. Dean could admit that Cas was a good-looking guy, but that was Jimmy's look; he had no idea what Castiel's true form was, and if what he was hearing was true, he probably had three heads, nine tails, claws for hands, and was as big as a skyscraper. This human form was much easier to behold.

 _Can I kiss an angel?_ he had to ask himself. He sort of already had, but Anna had been human then. This wasn't the same thing. If he could look past the vessel, he needed to humor a friend's request: his dying wish.

Dean threw his arms up and uttered, "Fine."

"Fine?"

Dean twisted on his heels to face Castiel, holding up a finger. "Once," he decided, putting his hands on his hips. "I'm not into dudes, but for you..." He pulled his lips into a tight line. "...Your whole life could be over in a few hours. It's a kiss. Nothing I can't handle. If it'll help you resolve some issues, lay one on me, my friend."

Castiel opened his hands and leaned forward. "If it helps, I am not a male in the sense that humans-" he started.

Dean shook his head and waved his hand in front of Castiel. "Doesn't help. Your meat suit is man. Deep voice. Stubbly beard. Kickstand. The package is all wrong for my liking." All wrong.

Castiel stood, staying in front of the chair, seeming to wait for permission to move forward. "The only current female of Jimmy Novak's bloodline is his daughter," he said, "I made a promise that I would not-"

"No, dude," Dean interrupted, vigorously shaking his head, "She's just a kid. That's a 'hell no'. That package is worse than Jimmy's." He took a step towards Castiel and pointed at the floor in front of him. "Just get over here, so we can get this over with."

Castiel did as he was told, coming forward before Dean. "What do I do?" he asked, sounding _almost_ eager. His tongue darted out to wet his lips.

Dean cleared his throat and told him, "It's not hard. Just do it."

He closed his eyes then, waiting for the feel of another man's mouth on his own, but it didn't come. He chanced squeezing one eye open to find Castiel simply contemplating his face with darting eyes, remarkably close, but otherwise, unmoving. Dean huffed and rolled his eyes; he'd have to be the one to initiate, so he puckered his lips and leaned forward, keeping his arms stiff at his sides. Castiel didn't meet him half way, and he still wasn't moving. Dean pressed his lips to Castiel's. Nothing. He pulled away with a quiet groan, and then he noticed the faint quivering of Castiel's fists clenched tightly at his thighs.

"Is that it?" Castiel asked quietly, his voice uncertain.

Dean gruffly responded, "It's not if you do it right. Open your mouth."

Castiel did as he was told.

"Not _right_ now," Dean corrected him. "When it feels right, you know?"

"When it feels right," Castiel repeated.

Dean nodded. "Yeah."

Dean leaned down again, watching Castiel's eyes flutter closed before he shut his own. Somehow, the angel appeared less rigid when Dean brushed his mouth over his lips this time. Dean pressed more firmly, and when Castiel parted his softening lips, Dean smirked into the beginning of their kiss. Neither of them were touching each other except where Dean's mouth moved gently against Castiel's. Dean applied more pressure so that Castiel had to tilt his head back slightly. Castiel sucked in a surprised breath when Dean's tongue pushed past the small slit between his lips.

Dean knew he didn't need to take it any further or for much longer, but he had promised his friend he wouldn't die a virgin. This was the least he could offer. He could almost ignore the mild scratch of stubble around his mouth with the warmth of Castiel's breath on his cheek. Dean hadn't been close enough to the angel to notice before, but his smell was something that he couldn't fully describe – it made him think of rain and fire and dirt. There was no artificial fragrance of perfume, cologne, or even soap. It was so familiar and unfamiliar all wrapped up together that the aroma of Castiel was worldly and otherworldly at the same time.

The problem was Castiel still wasn't actually responding in kind though; he had let Dean take the ropes, but unless he kissed back... Dean could lead a horse to water, but he couldn't make it drink.

Dean pulled back a fraction and harshly whispered, "You're going to have to give me something to work with."

Castiel swallowed and wet his lips again. "Something more?"

"Yeah, sure."

Castiel grabbed Dean by the collar of his jacket and pulled him rather roughly towards him. Dean's cry of surprised was muffled by Castiel smashing his mouth against Dean's. Dean was only slightly surprised when his first though was, _That's more like it._

He reached up, taking hold of Castiel's jaw between his hands, ignoring the prickle of scruffy beard on his palms. Castiel's grip on his jacket didn't loosen; he held Dean firmly in place, and he was actively participating this time. His lips puckered and moved against Dean's, hesitant but powerful. Dean had always enjoyed a woman with more experience, but this... this was sort of sweet. He grazed his tongue over Castiel's bottom lip, felt the man's hot breath on his mouth, and heard a quieted sigh escape.

Dean bit back a groan when Castiel's tongue cautiously met his own. Despite Castiel's inexperience, Dean thought kissing him wasn't too bad. If he only focused on their mouths, on the quickening breath playing across his mouth and cheeks, on the tongues grappling, on the muffled sighs. It wasn't a hurried kiss with a giggling girl that wanted to strip him out of his pants as quickly as possible. It wasn't a desperate world-ending kiss either. It was slow and exploratory but as chaste as it ever could be.

Castiel tasted like rain as Dean thrust his tongue deeper into the angel's mouth, trying to pull Castiel impossibly closer by his jaw. For a moment, Dean would swear they were outside with the heavy rain falling around them, but that was impossible. They were inside, and it was dry, but Castiel's mouth was hot and wet. Dean was sure his agreement to Cas was well covered by then, but he didn't know when to stop. He was somewhat terrified that he might not want to.

Abruptly, Castiel pulled back, his hands loosening their grip on Dean's jacket. He tilted his head as he took a step back, his gaze flitting from Dean's mouth to his eyes. "That was... not unpleasant," he admitted plainly.

Dean blinked, shaking his head to get a clearer picture of what was going on in his brain. "Uh, yeah," he found himself saying in agreement. "So..." Dean pursed his lips, uncertain of what he was supposed to say to an angel that he had just made out with. "...what now?"

Before Castiel turned away to the jar on the table, Dean caught the color and fullness of his lips. Normally so pale and tight, they were flushed and swollen from their kissing. It made Dean look for an invite to the party in his own pants, finding with relief that his party had barely started. Things were definitely warm and bubbly, but not so _excited_ that he'd have to go deal with it.

"You should get some sleep," Castiel told him while he sat back down into his chair. "I will wait here and prepare for Raphael."

Dean nodded, glancing into the depths of the house. "Back to business then."

"Yes."

Words failed Dean as Castiel returned to staring into nothingness. What Dean would have killed to have that exact _non_ -discussion with anyone else he had just spent the night with. Back to business. No climbing out the window before she woke up. No awkward, 'sure, I'll call you' before he lost her number. Dean realized that he was _disappointed_. Castiel's reaction might have meant that he didn't enjoy it – plenty of women would corroborate that Dean was a great lay, and that went for kisses – and it bothered Dean that Castiel was so calm and cool despite his previous anxiety at the brothel. It nagged at his ego a bit.

He worried over whether he should even ask Castiel what he thought besides 'not unpleasant'. Dean had felt that it had been _nice_. Dean was positive that his heterosexuality was still in check – he had no interest in jumping the man's bones after that – but kissing Castiel was... he just couldn't put his finger on it.

Dean mumbled a 'good night' in Castiel's general direction as he turned down the hallway for the comfort of a dusty couch. Unanswered questions were beginning to bubble to the surface, but Dean figured it would be best to deal with them later. If it was ever brought up again. For now, Castiel got a small taste of what he might be missing out on which was enough. Dean needed sleep, and the plan didn't require any actions until a few hours before sunrise.

While Dean waited for sleep, he missed Castiel in the other room grazing his thumb over his lips that were set into a slight smirk, eyes glazed over in reminiscence.


End file.
